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Chapter 18
by Mr Nice Guy
What's next?
The Purge
Riley held up the shirt like it was something half-dead. Faded navy blue, cracked graphic on the chest, sleeves that had probably never fit him right—it looked like something someone's dad would mow the lawn in. He sniffed it, winced, and turned to Isabelle.
"Why… why do I still own this?"
Isabelle beamed from her perch on the edge of his bed, legs crossed, one perfectly manicured hand flipping through a small pile of his old clothes like it was toxic waste. "That’s what I was wondering, sweet thing."
He tossed the shirt into the giveaway pile with a flick of his fingers, already half-embarrassed that she'd seen it. "I didn't even know I still had that. Seriously, that's disgusting."
"Exactly." She held up a pair of boxers—faded plaid, saggy waistband. "And what about these, princess? You planning to impress someone with these little nightmares?"
Riley groaned. "No! God, no. Burn them. Please."
He didn't feel upset. Not really. It was more like secondhand embarrassment for the person he used to be. The guy who wore chunky, outdated sneakers and didn't even exfoliate. What had he been thinking? No wonder he couldn't hold onto a relationship. Back then he was just… sloppy.
Going through his clothes, seeing what he had and what he needed, had been Isabelle's idea. She always had great ideas, things Riley hadn't thought of, things that always turned out to be great for him. Looking at the pile of clothes that he was getting rid of, he was genuinely surprised at how big it was. It had taken up almost half of his closet, not to mention far too many drawers. Now that he was rid of them, he felt like a snake shedding its skin. He was ready for his future, for the new Riley to blossom.
"How could I have expected anyone to want me when I looked like I didn't care at all?" he said, folding his arms and glancing at himself in the mirror—lashes curled, gloss shining. "Like, new Riley makes an effort. Old Riley was just a mess."
Isabelle smirked and stood, brushing her hands off like the purge was complete. "Exactly. You're putting in the work now, and it shows. But—" she pointed toward his desk, "clothes are only part of the story. If you're going to attract women, if you're going to end up as Chase's girlfriend, there's more to do."
Riley blinked. "The clothes are gone. What else is there? Do you mean shop for more?"
She strolled over, tapped on his laptop, and pulled up a browser window. It was already logged in. His social media. The feed was filled with memories—bad ones. Old gym selfies with protein shake captions, dorky birthday photos with guys he hadn't seen in a year, reposted memes that weren’t even funny. And the pictures… oh God, the pictures. Sloppy hair, awkward smiles, boxy shirts. The past staring back at him like a ghost in cargo shorts.
"We got rid of the old clothes," Isabelle said softly. "Now it's time to get rid of the old image."
He swallowed. "You mean… delete my socials?"
"Wipe them clean. Start fresh. Make a new account that shows off the real you. Not him," she said, pointing at a photo of him and his high school friends holding burgers with way too much enthusiasm, "but you. The Riley you’ve become. The one people want to know."
He hesitated. "But… I've had this account forever. Like, since ninth grade. I've got friends on there. People I actually know."
"And how many of them do you actually talk to anymore?" she asked gently. "How many of them would even recognize the Riley standing here right now?"
He didn't answer. He didn't have to. His silence said enough.
"They're just going to judge you, babe," she continued. "If they see those old photos, if they see how you used to be, it'll colour everything they think about you now. You deserve better than that. You deserve to be seen as you really are."
It made sense. It made too much sense. But it still felt like a betrayal—of who he'd been, of the people who’d known him back then. Even if that person was a mess… he was still him, once. Wasn’t he?
Riley bit his lip. "I… guess I could deactivate it? For now?"
Isabelle stepped closer, took his hand, and squeezed it gently. "I know it's hard. But this is about your future. Not your past. Don't let those old posts drag down the new you."
He nodded slowly, breathing in. His painted nails hovered over the keyboard. A few clicks. Settings. Delete account.
Confirmation.
It was done.
The screen went white for a moment. Then nothing. Riley felt hollow… and then light.
"You did the right thing," Isabelle said.
"Yeah," he said softly. "Yeah, I think I did."
Her face brightened. "Now—photoshoot time!"
"What?"
"You didn’t think I'd let your new online presence launch without the perfect profile pic, did you?" She grabbed her phone and motioned toward his closet. "Go on. I'll pick out a few outfits. Something cute, something casual, and definitely something flirty. We're building your personal brand, angel."
Riley laughed nervously. "I dunno, Isa… I don't really take good photos."
"Nonsense," she said, already thumbing through hangers of his remaining clothes. "You take amazing photos. You just need the right energy. Trust me. I'll pose you, light you, pick the filter. You just smile and be adorable."
He hesitated… but she hadn't steered him wrong yet. Isabelle was always right. Always.
"…Okay. Let's do it."
She turned, triumphant, holding up a cropped cardigan and a silky pair of white shorts. "Perfect. This'll scream 'modern, polished, irresistible.' You're going to break the internet."
Riley took the outfit, pressing it to his chest and watching himself in the mirror.
The old him was gone.
Now, with Isabelle's help, he had a real chance at something better.
What's next?
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jun 20, 2025
by Mr Nice Guy
Created on Feb 1, 2018
by Dayeandknight
- 4,658 Likes
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- 333 Chapters
- 40 Chapters Deep
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